Natural bitumens consist of many molecules whose chemical composition depends on the oilfield and determines the physicochemical properties of the bitumens as materials. Infrared (IR) spectroscopy is the fastest and least expensive method to assess the chemical structure of organic molecules, which makes it attractive in terms of rapid prediction of the properties of natural bitumens based on their composition evaluated in this way. In this work, IR spectra were measured for ten samples of natural bitumens significantly different in properties and origin. Based on the ratios of certain IR absorption bands, bitumens are proposed to be divided into paraffinic, aromatic, and resinous. In addition, the internal relationship between IR spectral characteristics of bitumens, such as polarity, paraffinicity, branchiness, and aromaticity, is shown. A study of phase transitions in bitumens by differential scanning calorimetry was carried out, and the use of a heat flow differential to find hidden points of bitumens' glass transitions is proposed. Furthermore, the dependences of the total melting enthalpy of crystallizable paraffinic compounds on the aromaticity and branchiness of bitumens are demonstrated. A detailed study of bitumens' rheology in a wide temperature range was carried out, and characteristic features of rheological behavior for different bitumen classes are revealed. Based on the viscous properties of bitumens, their glass transition points were found and compared with the calorimetric glass transition temperatures and nominal solid-liquid transition points obtained from temperature dependences of bitumens' storage and loss moduli. The dependences of viscosity, flow activation energy, and glass transition temperature of bitumens on their IR spectral characteristics are shown, which can be used to predict the rheological properties of bitumens.